72 Hours in Vermont’s Deerfield Valley
Two Nights and
Three Days in Vermont’s Deerfield Valley
Nestled in the southern reaches of the Green Mountains and conveniently located just a few hours from New York City and Boston, the Deerfield Valley offers a quintessential Vermont experience. This serene and scenic area is renowned for its unique shops, burgeoning art scene, vibrant farm-to-table dining, and a plethora of year-round outdoor activities, all set against the breathtaking backdrop of mountains. Unplug, unwind, and immerse yourself with this itinerary, offering a blend of adventure, relaxation, and authentic Vermont hospitality.
Visit At a Glance
These three days offer suggestions for things to do surrounding lodging, dining, shopping, and nearby attractions. Use this itinerary as a guide for further discovery – bookmark these locations and walk the downtown. Another great way to find a hidden gem is to ask a shop owner for their favorite local spot.
Key Points of Interest
Each day is comprised of shops, restaurants, and cultural attractions.
- Day 1: Begin your exploration of the Deerfield Valley immersing yourself in the diverse array of experiences offered, using Mount Snow as your basecamp.
- Day 2: Enjoy the day taking in the charming town of Wilmington.
- Day 3: Take a scenic drive along Vermont Route 100, known as Vermont’s “Main Street.”
Begin your exploration of the Deerfield Valley immersing yourself in the diverse array of experiences offered, using Mount Snow as your basecamp.
– DAY 1
Molly Stark Byway
Wind your way through the region’s valleys and historic villages and downtowns on Vermont’s southernmost byway. The Molly Stark Byway was named after the wife of General John Stark, who led the colonial militia to a victory at the Battle of Bennington on August 16, 1777.
First Trax
Stop at this family-friendly, customer centric shop, offering a diverse range of top-quality ski apparel and gear and expert fittings by industry veterans.
Memorial Hall Center for the Arts
Check out their screening schedule, featuring a diverse range of performances from Broadway cabaret to jazz and cinema screenings.
The Bullwheel
Upstairs in the Summit Lodge, delight in the flavors of Vermont with sharable dishes, hearty sandwiches, and a local draft list while enjoying the breathtaking views from the observation deck. Before your visit, please check the Mount Snow website for current hours of operation.
Last Chair Bar & Grill
Enjoy tender-aged steaks, unique pizzas, and locally brewed drafts, along with the Kid’s Zone arcade and a brand-new bar, all housed in a big red barn marked by a hanging lift chair.
Trail 87 Restaurant
A seasonally inspired menu highlights the finest of Vermont’s local produce, complemented by a diverse selection of craft beers, whiskeys, and wines.
Snow Republic Brewery
A veteran-owned production brewery, taproom, and kitchen, all in a pet- and kid-friendly atmosphere.
Grand Summit Resort
Discover Vermont-inspired comfort at Mount Snow’s Grand Summit Resort, offering charming rooms, suites, a full-service spa, fitness center, and slopeside convenience.
Mount Snow
Enjoy a day of exhilarating outdoor activities at Vermont’s largest southern ski resort, offering adventure during any season. In summer, enjoy hiking or mountain biking, and in winter, experience some of Vermont’s finest skiing, good for any level of skier.
Adaptive Sports at Mount Snow
Offering sports lessons and recreation for people with disabilities year-round, providing the opportunity for every body to enjoy skiing, snowboarding, snowshoeing, rafting, mountain biking, fly fishing, and more.
Enjoy the day taking in the charming town of Wilmington.
– DAY 2
Boyd Family Farm
In business for over 80 years, immerse yourself in the beauty of pick-your-own flowers and blueberries in summer, vibrant fall foliage, and festive winter wreaths, set against an idyllic backdrop.
Bartleby’s Books
Step into a beloved independent bookstore, where a treasure trove of new books, unique gifts, and local art awaits.
The Village Roost
Experience the unique blend of exceptional cuisine, a cozy and friendly atmosphere, and a commitment to sustainability. Every dish is crafted with organic ingredients, freshly baked bread, and house-roasted meats.
The Wilmington Inn
Enjoy the perfect blend of historical charm and modern amenities, complete with cozy, tranquil rooms, personal touches, and warm hospitality.
Take a scenic drive along Vermont Route 100, known as Vermont’s “Main Street.”
– DAY 3
Sprague & Son Maple
Enjoy year-round tours and tastings, witness the traditional maple sap boiling process, and savor handcrafted maple products all made on-site.
Hogback Mountain Country Store
A Vermont landmark since 1936, offering a vast selection of local specialty foods, apparel, and unique gifts, all set against the backdrop of a breathtaking 100-mile view from the scenic overlook.
Alpenglow Bistro
A cozy mountain retreat offering a taste of the Alps, a refined drink selection, and a warm, inviting atmosphere perfect for unwinding by the fireplace or on the patio.
Vermont Distillers
Sample and savor handcrafted, naturally gluten-free spirits including the Metcalfe’s family of liqueurs, Maple Bourbon, Honey Bourbon, and Catamount Vodka while taking in the sights of the Hogback Mountain Scenic Overlook.
The Engel House
Step back in time with a stay at this historic B&B, where the charm of an 1836 colonial farmhouse blends with modern comforts.
Molly Stark State Park
Hike the park’s trails, explore the Mt. Olga fire tower, and take in the breathtaking views of the Deerfield Valley.
Hogback Mountain
This Vermont landmark has offered a vast selection of local specialty foods, apparel, and unique gifts since 1936. Take in the breathtaking 100-mile view overlooking a vista encompassing Vermont, Massachusetts, and New Hampshire.
About the Vermont Inspiration Guide
This itinerary comes from the Vermont Inspiration Guide through a partnership between the Vermont Department of Tourism and Marketing and the Vermont Chamber of Commerce. This free annual publication highlights Vermont’s restaurants, retailers, attractions, and outdoor adventures and can be ordered online along with other trip planning resources.